


NSFW ALPHABET w/ Dean Winchester

by deanmonreigns



Series: Supernatural Writings [47]
Category: Supernatural
Genre: F/M, Headcanon, Reader-Insert, Reader-Interactive, Sex, Smut
Language: English
Status: Completed
Published: 2020-07-16
Updated: 2020-07-16
Packaged: 2021-03-04 19:21:45
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,100
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25311523
Author URL: https://archiveofourown.org/users/deanmonreigns/pseuds/deanmonreigns
Summary: For Witch_Of_Letters.WARNING this headcanon involves explicit gifs
Relationships: Dean Winchester/Original Female Character(s), Dean Winchester/Reader, Dean Winchester/You
Series: Supernatural Writings [47]
Series URL: https://archiveofourown.org/series/1833058
Kudos: 29





	NSFW ALPHABET w/ Dean Winchester




  * 


**A = Aftercare (What they’re like after sex)**

_Dean is really clingy after sex. He loves cuddling with you, especially spooning you. He just wants you close to his body. Holding you way too tightly while leaving kisses on your shoulder blade, collarbone, neck, and top of your head, forehead, and lips._

_A couple of times you’d tell him you can’t breathe, he loosens his grip a bit but then goes right back to hugging you tighter. You are pretty sure one day his hugging will be the death of you he has such a tight grip._

_Once you’s have finished your cuddle session, and deep chats or talking about random things._

_Dean is his vulnerable after sex. Asking if you enjoyed it and if he should improve, he is honestly a babbling mess that you have to kiss him to get him to shut up._

_“Baby, sh, you are the best lover inside and outside the bedroom that I ever had.” You confessed, looking at him while tracing the possession tattoo with your finger._

_Which makes him smirk._

_“Yeah?” he questioned, smirking at you._

_“Yep.” You hummed, as Dean rolled on top of you, smiling at you._

_You and Dean will go to the shower to clean up. Sometimes you and Dean are lazy and he just gets a warm wet washcloth to clean you up.  
_**B = Body part** **(Their favourite body part of theirs and also their partner’s)**

 _Dean’s favourite body part of his has to be his hands_ _. Oh and that mouth of his. He knows that those two things please you the most._

 _Dean’s loves every part of your body, though his favourite parts have to be your boobs and ass, also your mouth damn your mouth makes him so many have dirty thoughts._ **  
C = Cum (Anything to do with cum basically… I’m a disgusting person)**

 _Dean loves to lick your cum off his also suck it off his fingers, not to mention_ _he loves it when you cum in his mouth and on his fingers._

_Dean knows he shouldn’t do it all the time but he can’t help but cums inside of you, he gets it’s a risky move and might get you pregnant one day, but he knows you take the pill, sometimes he forgets to put a condom on since he is so invested in the moment, though he does use a condom most times. In the moment he doesn’t really care if he forgets to pull out the feeling of your walls tightening around his cock brings his climax so much closer. Seeing his cum dripping out of your pussy is such a turn on._

_However, when he does pull out he cums on your stomach or your boobs, and on your pussy._

_He also cums in your mouth and on your face._  
**D = Dirty Secret (Pretty self explanatory, a dirty secret of theirs)**

_Dean has many dirty secrets some sexual, some just plain weird and some dark_ _._ _Though his biggest one is that he is a sub. He honestly loves it when you dominate him in bed and take charge. It turns him on when you ride him and take control. He even daydreams about it. Though he will never tell you._

**E = Experience (How experienced are they? Do they know what they’re doing?)**

_Dean is defiantly experienced in the bedroom, considering his flings and hook-ups plus relationships with women he has had in the past he is a pro at making women feel pleasure and orgasm. He knows what he is doing, and has learned techniques on the way._

_Though you do get insecure about the women he has been within the past, thinking that they were way better than you were and that you aren’t that good. While thinking about how he pleased them._

_However Dean begs to differ, telling you aren’t like you and you are entirely different to them, and that he loves you more than them and that they will never hold a flame to you {however that saying goes}/ no one holds a flame to you, how he doesn’t think about his past hook-ups while he is pleasuring you and how you are pleasuring him though that doesn’t make you feel better…_

_Instead of fighting with you about that he decides to show you how much you mean to him and how you are the only woman he thinks about/ loves._

_He can defiantly please you and make you writhe under his touch. He is an expert at making you orgasm and he has never failed at it. He is defiantly a pro with that mouth and hands/fingers of his, whenever he uses them you always end up gripping the bedsheets in a writhing moaning mess, not to mention he always hits your gspot every time, with his fingers and his dick._

**F = Favourite Position (This goes without saying. Will probably include a visual)**

_Dean loves sex, and he as a ton of favourite sex positions…'_

__

_Reverse cowgirl; Dean loves it when you are on top of him taking control, his inner sub shines through, plus it gives him a nice view of your ass. And he defiantly loves your ass, and grabbing a hold of it. Placing your hand in front of you as you slowly move up and down on his cock, making him moan in total bliss. Whenever you thrust into him, he will grab your ass and squeeze it hard or spank it, making you let out a moan. Not to mention when you play with his balls, it makes him moan loudly while his head falls back onto the pillow closing his eyes as his hands fall down to your thighs grabbing a hold tightly. While you talk dirty to him._

__

_Riding him; like reverse cowgirl he loves it when you are on top of him taking control. This move makes his dirty secret come out just a tad bit. Okay a lot, he is totally in awe as you ride him. Your boobs bouncing with every thrust, your hands resting on his chest as he grabs your boobs, squeezing them, then massaging them. Your head tilting back as you moan his name. Talking dirty talk to him, as your thrust get deeper. Dean can’t help but tilt his head back his eyes squeezing shut as the feeling of your walls tightening around his cock brings him closer to his climax, he tries to delay his release but you egg him on. Sometimes you cum after him other times you don’t which is when he changes positions and takes the lead, edging you closer to your orgasm._

__

_Missionary {in different variations};_

_Dean enjoys this position greatly, many reasons being he gets to see your facial expressions as he thrusts into you. Seeing your head tilt back onto the pillow with your eyes closed and your mouth a gap, while you let out tiny moans and gasps while your boobs bounce with every thrust is a beautiful fucking site._

_Though he prefers it when your eyes are open and you are looking at him when you orgasm. But he doesn’t mind it when your eyes are closed._

_Not to mention he gets full access of leaving love bites on your neck, shoulders, and collarbones._

_Also this position is great for putting one of your legs over his shoulder, while he thrusts in and out of you, not to mention putting both his hands on either side of your body while thrusting into you, though he prefers to press his whole body weight onto you, not fully he doesn’t want to squish you as he is fucking you._

__

_Lotus {sitting up sex}; this position makes you orgasm a lot faster than the other ones do. Like reverse cowgirl and riding him, you are the one on top, as he sits on the backseat of the Impala. Wrapping your legs around his waist and your arms around his neck, as you slowly rock yourself back and forth on his cock, his hands gripping your waist as you’s two make out._

__

_Against the wall; Dean uses this position when he is jealous or angry either one mostly when he is angry. Either a hunt going wrong or some civilian trying to be the hero, or_ _when you’s have a bad fight_

__

_Doggy style; Like fucking you against the wall he uses this move when he is jealous/angry, or when nothing goes his way, or a hunt goes wrong, or when you’s two have a bad fight._

_Pressing your face against the mattress as he thrust into you roughly, tugging on your hair and yanking your head back. His other hand gripping your waist harshly, sometimes even spanking you hard on the ass with each thrust._

_Growling into your ear, while nibbling on it. Talking really filthy things to you._

_He’ll leave love bites on your neck and shoulders._

_Every thrust hitting your gspot, your moans fuel him on even more. Especially when you turn your head to look at him, gasping and moaning, it just drives him closer to the edge._

**G = Goofy (Are they more serious in the moment, or are they humorous, etc)**

_Honestly, it depends on if he is fucking you or making love to you._

_When he is fucking you he is pretty much serious in that moment, though he might crack a few jokes after woods._

_But when he is making love to you then he will mostly tell you horrible cheesy pickup lines. Him and those bloody cheesy pickup lines._

_“Dean, I’m already your girlfriend stop using pickup lines on me while you are inside of him.” you huffed, as he chuckled._

_“Okay.” he muttered, continuing to thrust into you._

_“Hey y/n.” Dean spoke, into about a minute of thrusting, distracting you from your orgasm arising._

_“What?” you huffed, opening your eyes and giving him an annoyed look._

_“Are you a banana? Because I find you a-peeling.” Dean smirked, making you give him a bitch look. Dean’s smirk dropped into a frown._

_“Okay, I’ll stop.” He mumbled, going back to his slow deep thrusts._

**H = Hair (How well groomed are they, does the carpet match the drapes, etc.)**

_Dean honestly doesn’t care that much about grooming down there, but if you suggest it though he will do it, he will do anything for you. However, when he gets jealous and insecure he gives it a bit of a trim. The carpets match the drapes._

**I = Intimacy (How are they during the moment, romantic aspect…)**

_Dean loves to hold your hand tightly as he thrusts into you and when he eats you out/fingers you._

_Also, he leaves soft kisses on your shoulders, neck, collarbones, cheeks and your lips._

_Telling you how much you mean to him and how much he loves you._

**J = Jack Off (Masturbation headcanon)**

_Dean is a very horny man, and sometimes when you aren’t there to satisfy his needs or when you’s fight and you’s aren’t ready to talk it out, he masturbates. Laying down on the bed._

_Listening to the rock playlist he made, or he either watches porn, picking one with a women that kind of looks like you, taking out his throbbing cock from his sweatpants/jeans, as he strokes his cock as his thumb rubs against his swollen red tip, precum already leaking out, as his eyes are fixated on the screen as the porn plays out, playing with his balls lightly while moving his hand moving up and down slowly on the base of his cock._

_If he isn’t watching porn then he will close his eyes imagining it’s your mouth instead of his hand._

**K = Kink (One or more of their kinks)**

_Dean has many kinks, the one you don’t know about is how he is a sub, though you have a tiny suspicion that he may like to get dominated when you are on top of him._

_Dom kink, light bondage, huge daddy kink, Sir kink {if that’s a thing}, food play, he loves to_

_Dean defiantly has a praise kink, hearing you praise him or saying “oh my gosh, dean, yes yes yes.”_

_Just boasts that ego of his up._

_Light choking, spanking, Hair pulling, biting kink._ _Roleplay, Dean is a sucker for roleplaying._

_Rough sex, Sensation play, Orgasm control, Food play & Voyeurism._

**L = Location (Favourite places to do the do)**

_In the Impala, he loves fucking you/making love to you and doing other sexual activities in baby, especially in the backseat and the hood of the Impala, on a bed, mostly his bed or yours, but more his bedroom. Against the wall, hotel rooms, in the shower. Though if a hotel you’s stay at has a bathroom then he will defiantly fuck you/make love to you in there. On the kitchen table/ bench, though a couple of times Sam has caught you’s in the act, telling you’s how gross you’s are and how unsanitary fucking on a table is and how he has to eat there._

_“What a mood killer.” Dean grumbled, still inside of you._

**M = Motivation (What turns them on, gets them going)**

_Lots of things motivate Dean, he is always horny, and if you wear something tight, revealing or you are teasing him or trying to seduce him then it turns him on._

_What really motivates him is pleasuring you._

**N = NO (Something they wouldn’t do, turn offs)**

_Like I said in demon!dean, threesomes with other men, he doesn’t mind threesomes with other women and you, but when you mention having it with other men, mostly Castiel, is when he starts to get jealous._

**O = Oral (Preference in giving or receiving, skill, etc)**

_Dean is a giver. He loves to pleasure you to the point you are a writhing trembling mess._

_Like I said in experience dean was had many past relationships & hook-ups so he knows how to pleasure you, and he knows what he is doing, he knows all the techniques and tricks. He is a pro at using his mouth and fingers. With every lick and stroke of his touch, it makes you writhe, grab the bedsheets, moaning his name as you tilt your head back._

_Hearing you moan/moan his name as he eats you out/or/fingers you is such is such a huge turn on also it boasts that ego of his up._

_Though he defiantly has learned new things along the way._

_Dean also likes receiving oral too._ _He loves it when you give him a blowjob. To him you are the best women ever to give him a blowjob, which also makes you more confident when you give him a blowjob. You always seem to tease him whenever you go down on him, playing/massaging his balls and swirling your tongue around the tip of his cock._

_Which is when he whines and begs for you to just suck him already._

_“Please babe, just suck me.” He whined._

_When you finally stop teasing him and put his cock in your mouth, and start to bob your head up and down at a really slow pace. This is when he gets a bit rough pulling/tugging your hair way too hard, bucking his hips into your mouth and making you gag._

_What is even more pleasurable when you give him blowjobs is when you look at him while bobbing your head up and down._

**P = Pace (Are they fast and rough? Slow and sensual? etc.)**

_Depending on what mood he is in, he is either both fast and rough, as well as slow and sensual._

_Dean is fast and rough when he is in an angry/ jealous mood, leaving bruises on your shoulders, neck, and jawline, also your waist. His thrusting rough and deep, and fast talking really filthy things into your ear, while cocking you, not to tight enough for you to breathe. After woods he will apologize to you, hugging you closer to his body and pressing soft kisses on the top of your head, as well as your cheeks, and shoulders and neck._

_He is slow and sensual when he nearly lost you in a hunt, or when he is in the mood to make love to you, or one of you needs comfort of some sort then his pace is slow and sensual, his thrusts deep but slow, this is where he is more affectionate, kissing you softly on the lips, as well as your shoulders, neck, and collarbones. Holding your hand and telling you how much he loves you. As well as giving you compliments and talking dirty._

**Q = Quickie (Their opinions on quickies rather than proper sex, how often, etc.)**

_He loves them, though he does love taking his time pleasuring you, he would never decline a quickie with you. But if you or him are in need of a quick fix and don’t have the time to have proper sex then a quickie it is. Most of the time you’s have a quickie once a day or twice depends._

**R = Risk (Are they game to experiment, do they take risks, etc.)**

_Dean isn’t afraid of experimenting and taking risks in the bedroom. Though he normally asks you first before he tries something new, just to see if you are okay with it._

**S = Stamina (How many rounds can they go for, how long do they last…)**

_Dean can last all night long, given a few breaks along the way. Though you normally get tired after about the fourth-five round, gasping for air while Dean gets ready for another round._

**T = Toy (Do they own toys? Do they use them? On a partner or themselves?)**

_Dean uses handcuffs, blindfolds and a vibrator on you._

_Though he does like it when you handcuff him to the bedpost, or use a scarf and take control._

**U = Unfair (how much they like to tease)**

_Dean is such a huge tease. The biggest tease in the world. Whether it’s sexually or none sexually he pretty much loves to tease you._

_He likes to touch you in public or when you’s are interviewing witnesses his hands resting on your thigh, slowly inching its way up. Which makes you excuse yourself from the conversation and drag Dean with you and scolding him though he denies that he did anything wrong acting innocent._

_If you’s are standing then he will rest his hand against your ass, grabbing it, while smirking, making you choke on your words, course Dean being the smug little shit he is he continues on what you were saying while touching your ass still._

_If he has a lollipop then he’ll defiantly tease you with that, licking it sexually as he eye fucks you._

_He defiantly sends you dirty texts._

_Touching/paying attention to every part of your body except for your wet core. He loves to delay your orgasms as well. Tsking you when you whine._

_You always seem to be in a hot begging mess when he teases you and seeing that boosts his ego up also makes him feel proud of himself._

_He loves to tease when you are researching, standing behind you and wrapping his arms around you while leaning down, his mouth close to your ear as he whispers dirty things into your ear as well as dirty fantasies he is going to do to you, he even leaves kisses on your neck._

**V = Volume (How loud they are, what sounds they make)**

_Dean is a very vocal man when he has sex, he doesn’t even think about it he just makes the sounds, and he doesn’t really care how loud he is. The louder you moan the better. His moans are like music to your ears. Also, your moans and sighs are music to his ears._

_Most of the sounds he makes are moans, grunts, growls, and words even sighs._

_He loves to tell you how you good you feel against him, and how much he desires you/loves you._

**W = Wild Card (Get a random headcanon for the character of your choice)**

_Dean glared at the guy that was flirting with you, his glare intensify’s as the guy had the nerve to put his god damn filthy hand on your thigh, caressing your thigh softly._

_He should be the only man to touch you like that. Dean stood up abruptly, clenching his fist, just as he was about to walk Sam grabbed his forearm making dean look at him, a glare still on his face._

_“Dean, if you go over there now you are going to wreck the whole plan.” Sam tried to reason with him._

_“I don’t care about the fucking plan he just touched my girl, no one touches my baby, no one, I’m going to kill him.” Dean grumbled, looking back at the scene._

_“I thought the Impala was your baby?” Sam asked Dean turned his attention to Sam furrowing his eyebrows._

_“They are both my baby’s, that’s not the point he touched my baby, now he must pay.” Dean grumbled, getting out of Sam’s grip and taking a step forward._

_“Dude, relax, you are going to wreck the plan.” Sam spoke, resting his hand on Dean’s shoulder._

_“Relax? He is trying to get in my girlfriend and stuff the plan.” Dean growled, giving his brother an annoyed look._

_“Just wait until she gets him outside then you can go all crazy on his ass.” Sam spoke. Though Dean didn’t seem to be listening he was too busy glaring at the guy that was touching his girlfriend._

_“Dean, are you even listening to me?” Sam asked, snapping his fingers in front of Dean’s face._

_“That’s it.” Dean snapped, pushing past his brother and storming his way over to you and the dickhead._

_“Get your hands off my girlfriend, you dick.” Dean growled, shoving the guy off the bar stool. The guy fell on the floor, making Dean climb on top of the guy and punching his face repeatedly, you tried to coax Dean into stopping and getting off the guy before he got kicked out but Dean was in a trance._

_“Good going Dean, wreck the whole entire plan because you can’t control your jealousy.” Sam muttered making his way over towards the scene. Sam grabbed Dean off the guy, with a little help from you dragging him outside._

_Dean tried to walk around Sam, his eyes filled with anger but Sam stopped him._

_“Stop, Dean you’ve done enough.” Sam grumbled Dean turned around only to face you, glaring at him._

_“Dean, what the hell?” you snapped at him, making Dean let out an annoyed huff.  
“He was flirting with you and touching you inappropriately only I’m allowed to flirt with you and touch you like that.” Dean defended himself, making you roll your eyes._

_“That doesn’t mean you had to punch him repeatedly.” You grumbled, making Dean rolling his eyes._

_“I’m not going to apologize for punching him, he had it coming.” Dean grumbled, turning around and walking away._

_Sam gave you a small smile, while you pinched the bridge of your nose before letting out a sigh._

_“I’ll go after him.” you huffed…_

**X = X-Ray (Let’s see what’s going on in those pants, picture or words)**

_Like I said in demon!dean, he may not be the biggest or the longest/largest but he is defiantly thick. And you telling him that he is the biggest you’ve ever been with and the greatest defiantly boast his ego._ ****

**Y = Yearning (How high is their sex drive?)**

_Oh so high, Dean is basically in the mood for sex all the time. He is always horny when he is around you, or thinking about you. He can’t help it and yeah sometimes his mind does wonder_

_You’s have sex at least 4-5 times a day, even more, Dean is just addicted to you, you’re his drug and he needs his fix._

**Z = ZZZ (… how quickly they fall asleep afterwards)**

_Dean doesn’t fall asleep quickly. Since he is protective over you. He likes to watch over you, holding you close to his chest, while rubbing soothing circles on your back or your shoulders. Pressing soft kisses against the top of your head, your forehead then your lips._

_He can’t help but fall more in love with you._

_Once he knows you are fully asleep he will then tell you all the things he can’t tell you to your face, too afraid to tell you or just insecure to talk about._

_Though eventually sleep sets in and he drifts off to sleep._


End file.
